CN105188404A

CN105188404A - Emulsifier composition

Info

Publication number: CN105188404A
Application number: CN201480027092.0A
Authority: CN
Inventors: F.V.斯帕索; A.K.K.劳森
Original assignee: Danisco US Inc
Current assignee: DuPont Nutrition Biosciences ApS; Danisco US Inc
Priority date: 2013-05-13
Filing date: 2014-05-07
Publication date: 2015-12-23
Also published as: JP2016523522A; EP3001798A1; WO2014184079A1; BR112015026609A2; US20160073663A1; GB201308502D0; MX2015015604A

Abstract

There is provided an emulsifier composition comprising (a) a diacetyl tartaric acid ester of mono- and diglycerides (DATEM); (b) free acetic acid in an amount of less than 0.4 wt% based on the amount of DATEM; and (c) a salt or base, wherein the salt or base is capable of donating a metal ion to one or more carboxyiic acids present in the DATEM to form a salt of the carboxyiic acid present in the DATEM, wherein the salt or base is present in an amount to provide a degree of neutralisation of at least 0.25 mol %.

Description

Emulsifier combination

The present invention relates to a kind of stable deodorization emulsifier combination, prepare the purposes of the method for said composition and the material for stable deodorization emulsifier combination.

Diacetyl tartrate (DATEM) that is single and two glyceride is a kind ofly widely used in the powerful emulsifying agent curing application.DATEM is curing the market that the application in industry is a relative maturity, and its use amount is large and stablize.If the major defect of DATEM can be overcome, just can suppose that DATEM has the great potential being applied to and curing outside industry.This shortcoming is the characteristic odor that DATEM has acetic acid.

The invention solves the problem that the DATEM that can use in the application very sensitive in the characteristic odor for acetic acid is provided.Specifically, the present invention relates to the odorless DATEM providing and there is several months extended storage stability, be desirably 6 months or more for a long time or 12 months or more of a specified duration.

From prior art, the acetic acid odor of DATEM can be removed by steam deodorization procedures, and do not affect the function of DATEM.Can by operation or series-operation carry out deodorization in batches.Free acetic acid amount can be generated by these operations and be less than 0.4%, be less than the product of 0.1% ideally.But As time goes on these deodorant products known can discharge free acetic acid gradually, and characteristic acetic acid odor can be produced once again.The invention solves the problem making the DATEM product of deodorization stable, make it can not produce rapidly characteristic acetic acid odor once again.

The present invention alleviates the problem of prior art.

In one aspect, the invention provides the emulsifier combination comprising following composition:

The diacetyl tartrate (DATEM) of (a) list and two glyceride;

B (), based on the gauge of DATEM, is less than the free acetic acid of the amount of 0.4 % by weight; With

C () salt or alkali, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM, and to form the salt of the carboxylic acid be present in DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.

In one aspect, the invention provides the method preparing emulsifier combination, described emulsifier combination comprises following composition:

The diacetyl tartrate (DATEM) of (a) list and two glyceride;

(c) salt or alkali, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM, and to form the salt of the carboxylic acid be present in DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%,

The method comprises

I) diacetyl tartrate (DATEM) that is single and two glyceride is provided;

Ii) optionally deodorization is carried out to DATEM, make DATEM comprise gauge based on DATEM, be less than the free acetic acid of the amount of 0.4 % by weight; With

Iii) at step I i) before or after, DATEM and salt or alkali are merged, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.

In one aspect, the invention provides the purposes of the diacetyl tartrate (DATEM) for stable list and two glyceride of salt or alkali, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM.

In one aspect, the invention provides the purposes for reducing or suppress the middle acetic acid release of the diacetyl tartrate (DATEM) of list and two glyceride of salt or alkali, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM.

In one aspect, the invention provides a kind of emulsifier combination as fully described in conjunction with example.

In one aspect, the invention provides a kind of method as fully described in conjunction with example.

In one aspect, the invention provides a kind of purposes as fully described in conjunction with example.

We surprisingly find, if by adding salt or alkali forms acetic acid further in DATEM composition, then deodorization DATEM composition can be made to stablize, described salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM.The metal ion contributed by described salt or alkali can form the salt of the carboxylic acid be present in DATEM.

The invention provides the mode for stablizing DATEM composition after deodorization.This allows people's long term storage DATEM composition, and can not produce or occur unacceptable acetic acid odor once again.In this way, DATEM composition can be used in those applications that in the past cannot use due to acetic acid odor.

For ease of consulting, existing discuss under suitable chapter title of the present invention in these and more in.But the description under each chapters and sections may not be confined to each concrete chapters and sections.

Detailed description of the invention

As described herein, the invention provides a kind of emulsifier combination, described emulsifier combination comprises the diacetyl tartrate (DATEM) of (a) list and two glyceride; B (), based on the gauge of DATEM, is less than the free acetic acid of the amount of 0.4 % by weight; (c) salt or alkali, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.

DATEM

As mentioned above, diacetyl tartrate (DATEM) that is single and two glyceride is known emulsifying agent.These emulsifying agents are regarded as safe usually, and can be prepared by multiple diverse ways.

Methods known in the art (such as with method disclosed in Publication about Document) can be used to prepare DATEM of the present invention.Earlier patents description US-A-2236516 (people such as FrankJ.Cahn) discloses and reacts by diacetyl tartaric acid and glycerin monostearate the product obtained.US-A-2689797 (MorrisH.Joffe) discloses the diacetyl tartrate of list and/or partial glyceride by mixing unsaturated and fractional saturation and the improvement that bread is obtained.US-A-2938027 (MartellM.Gladstone) discloses the reaction between the mixture of the acetylation acid anhydrides of food acid and the partial glyceride of aliphatic acid; described food acid is such as containing the tartaric acid of 4% to about 95% diacetyl tartaric acid and such as free acetic acid acid anhydride, can be obtained the product of improvement by described reaction.US-A-3443969 (people such as NobuoNakejima) discloses the diacetyl tartrate of the monoglyceride of (molecular clock) vegetable oil of purifying.GB-A-1220488 (AktieselskabetGrindstedvaerket) discloses the preparation process of emulsifying agent, described emulsifying agent reacts under specific mol ratio by making the glycerin monostearate that such as distills and diacetyl tartaric anhydride, then long-time heating obtains to 135-190 DEG C, gratifying HMW oil-water emulsifiers is obtained through polymerization, this emulsifying agent is separated with water owing to making acetic acid, so obviously comprise polyester.GB-A-1344518 (Dynamit Nobel AG (DynamitNobelA.G.)) discloses the solid acetyltartaric acid esters being reacted gained by least part of acetylizad tartaric acid and partial glyceride; described partial glyceride comprise the monoglyceride of 55-65% and iodine number lower than 5, every mole of partial glyceride comprises the tartaric acid residue of 0.91-1.8 mole and the acetic acid residue of 1.8-3.4 mole.These esters are free-pouring powder, and traditional ester has the denseness of class ceraceous or honey.EP-1016647 (Quest International B.V (QUESTINTERNATIONALB.V.)) describes the operation with two steps: in step one, generate the winestone acid anhydrides of purifying, then, in step 2, the monoglyceride of described winestone acid anhydrides and distillation and odium stearate are reacted.Obtain the product that degree of neutralization is 0.21%.US-2012/0058232 (GaofengLiu, ShumingYu) describes and carries out esterification in case by depositing at SPA, prepares the method that degree of neutralization is the list of 0.09% and the diacetyl tartrate of two glyceride.

Diacetyl tartrate of the present invention can be prepared by monoglyceride and single double glyceride, described single double glyceride contains the monoglyceride based on commercially available grease meter 40%-99%, and described commercially available grease comprises the full of different chain length (C8-C22) and/or unrighted acid.Tartaric amount is usually between 10% and 35%.In some respects, DATEM can containing being used as the glyceryl ester expanding agent.

For monoglyceride, the suitable glyceride stock that list-double glyceride and glyceryl ester expand agent is selected from but is not limited to unrefined, refining, hydrogenation, the grease in the animal or plant source of partial hydrogenation or fractionation, such as, but not limited to apricot kernel oil, babassu oil, butter, chicken fat, castor oil, cupu oil, coconut oil, cottonseed oil, evening primrose oil, fish oil, hazelnut oil, mist ice grass grease, kokorm, lard, linseed oil, corn oil, mango, herring oil, olive oil, palm-kernel oil, palm oil, peanut oil, rapeseed oil is (high, low erucic acid), rice bran oil, safflower oil, high oleic safflower oil, seal oil, sesame oil, butter fat, soybean oil, high gas oil ratio soybean oil, sunflower oil, high oleic sunflower oil, tall oil, butter, tung oil, algae oil, unicellular alga oil, and the mixture of arbitrarily oil and/or fat in these oil and/or fat.

By the chemical constitution of Main chemical component DATEMI to the IV of DATEM, DATEM can be described.In addition, DATEM composition can comprise unreacted monoglyceride and list-double glyceride and glyceryl ester.

Wherein R is fatty acid chain.Typical fatty acid chain is C4 to C28 chain that is saturated or that comprise one or more degree of unsaturation.This document describes typical aliphatic acid.Each DATEMI-IV molecule has position isomer, and wherein each substituting group or the free hydroxyl group position in glycerol backbone may be different.

It will be appreciated by those skilled in the art that each DATEMI-IV molecule comprises at least one and can carry out with such as undefined salt or alkali the carboxylic acid that neutralizes.

deodorization

As described herein, composition of the present invention comprises the gauge based on DATEM, is less than the free acetic acid of the amount of 0.4 % by weight.So a small amount of acetic acid carries out deodorization process acquisition to DATEM subsequently by synthesis DATEM usually.But, one skilled in the art will appreciate that and use suitable method can synthesize the DATEM that free acetic acid amount is less than 0.4 % by weight.Therefore, in the method for the invention, the diacetyl tartrate (DATEM) of list and two glyceride is provided in one aspect; Then optionally deodorization is carried out to DATEM, make it comprise gauge based on DATEM, be less than the free acetic acid of the amount of 0.4 % by weight.In one aspect, deodorization is not carried out.In yet another aspect, deodorization is carried out to DATEM, make it comprise the free acetic acid of aequum, namely based on the gauge of DATEM, be less than the free acetic acid of the amount of 0.4 % by weight.

In one aspect, in emulsifier combination, the amount of free acetic acid is be less than 0.3 % by weight based on the gauge of DATEM, and the gauge such as based on DATEM is less than 0.2 % by weight, is less than 0.1 % by weight, is less than 0.05 % by weight, is less than 0.04 % by weight, is less than 0.03 % by weight, is less than 0.03 % by weight, is less than 0.01 % by weight.

Deodorising process should be interpreted as the process less desirable smell or volatile component such as acetic acid removed from product.Usually by (under usually maintaining the absolute pressure of 0.1-10kPa) under vacuo, steam (based on product meter usually between 0.01 % by weight to 2 % by weight) can be passed in product and carry out deodorising process.Heat product to the temperature being suitable for evaporating undesirably component.For acetic acid, this temperature is usually between 100 DEG C to 180 DEG C.By carrying out this process with continuous processing in batches.

stabilizing agent

One skilled in the art will appreciate that the salt or alkali that comprise in the compositions of the present invention for stable said composition.In one aspect, the salt for stable said composition is comprised in the compositions of the present invention.In one aspect, the alkali for stable said composition is comprised in the compositions of the present invention.Described salt or alkali can as stabilizing agents.As described herein, described salt or alkali can for one or more carboxylic acid donate metallic ions existed in DATEM, and to form the salt of the carboxylic acid be present in DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.

As described herein, in one aspect, the invention provides the purposes for reducing or suppress the middle acetic acid release of the diacetyl tartrate (DATEM) of list and two glyceride of salt or alkali, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM.In this respect, described salt or alkali are preferably to provide the amount of the degree of neutralization of at least 0.25mol% to exist.

Those skilled in the art can select salt or alkali by the carboxylic acid be present in DATEM known to it.We surprisingly find, by neutralizing the carboxylic acid be present in DATEM, can suppress the formation of free acetic acid.Be not bound by theory, it is believed that the release of the existence meeting catalysis acetic acid of carboxylic acid, and by this release can be reduced with carboxylic acid in neutralization or part.

In preferred at one, salt or alkali (c) can for the carboxylic acid donate metallic ions existed in DATEM product, and described DATEM product is selected from DATEMI, DATEMII, DATEMIII, DATEMIV, its position isomer and composition thereof.In preferred at one, salt or alkali (c) can for the carboxylic acid donate metallic ions existed in DATEM product, described DATEM product be selected from DATEMI, DATEMII, DATEMIII, DATEMIV, and composition thereof.

Preferably, the alkali that alkali (c) is metal, described metal is selected from the 1st race of the periodic table of elements, the 2nd race and Al of the periodic table of elements.Preferred metal is selected from lithium, sodium, potassium, magnesium, calcium and aluminium.Preferred metal is selected from sodium, potassium, magnesium and calcium.Preferred metal is selected from magnesium and calcium.Preferably, alkali (c) is the alkali of calcium.Preferably, alkali (c) is the alkali of magnesium.

One or more counter ion counterionsl gegenions of alkali are preferably hydroxide ion.Preferred alkali is NaOH, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminium hydroxide.Most preferably, alkali (c) is magnesium hydroxide.

One skilled in the art will appreciate that salt is formed by alkali and acid reaction usually, or formed by slaine and acid reaction, the described pKa value with the acid of reacting metal salt is higher than the acid be neutralized.In one aspect of the invention, salt (c) is the salt that alkali and carboxylic acid reaction are formed.In one aspect of the invention, salt (c) is slaine and is present in DATEM the salt having and formed compared with the acid reaction of low pka values.When salt (c) is the salt of metal and acid generation, this salt (c) is slaine, and it can be one or more carboxylic acid donate metallic ions existed in DATEM, to form the salt of the carboxylic acid be present in DATEM.

Preferably, the salt that salt (c) is metal, described metal is selected from the 1st race of the periodic table of elements, the 2nd race and Al of the periodic table of elements.Preferred metal is selected from lithium, sodium, potassium, magnesium, calcium and aluminium.Most preferably, salt (c) is calcium salt.

As for the acid that can form salt (c), it typically is organic acid.Preferably, salt (c) is monocarboxylic salt.In another is preferred, salt (c) is the salt of acid, and described acid is selected from formic acid, acetic acid, propionic acid and lactic acid.In highly preferred, the salt that salt (c) is acetic acid.

Preferably, salt (c) is the salt of (i) metal, and described metal is selected from lithium, sodium, potassium, magnesium, calcium and aluminium, and the salt of (ii) acid, described acid is selected from formic acid, acetic acid, propionic acid and lactic acid.Preferably, salt (c) is the salt of (i) metal, and described metal is selected from sodium, potassium, magnesium and calcium, and the salt of (ii) acid, described acid is selected from formic acid, acetic acid, propionic acid and lactic acid.Preferably, salt (c) is the salt of (i) metal, and described metal is selected from lithium, sodium, potassium, magnesium, calcium and aluminium, and the salt of (ii) acid, described acid is selected from acetic acid and lactic acid.

The combination of particularly preferred metal and acid provides following salt-calcium acetate, sodium acetate, magnesium acetate, magnesium lactate, potassium acetate, aluminium acetate and composition thereof.The combination of preferred metal and acid provides following salt-calcium acetate, sodium acetate, potassium acetate, aluminium acetate and composition thereof further.In highly preferred at one, salt (c) is at least calcium acetate or is made up of calcium acetate.

Most preferably, alkali or salt (c) are selected from magnesium hydroxide, calcium acetate, sodium acetate, magnesium acetate, magnesium lactate, calcium lactate, potassium acetate, aluminium acetate and composition thereof.Most preferably, alkali or salt (c) are selected from magnesium hydroxide, calcium acetate, sodium acetate, magnesium acetate, magnesium lactate, potassium acetate, aluminium acetate and composition thereof.

In a preferred embodiment, the part (i.e. counter ion counterionsl gegenions) for metal ion in salt or alkali can form acidity or neutral molecule, such as, but not limited to carboxylic acid (as acetic acid), water or CO ₂, in deodorisation process subsequently, remove these molecules by such as release or decomposition.

Salt can any suitable amount exist to provide stabilization.

The degree of neutralization based on the tartaric molar basis used in DATEM preparation process is used to calculate the amount of the stabilizing agent existed.Degree of neutralization can be defined as the molar percentage that the tartaric acid for the preparation of DATEM is neutralized by stabilizing agent.Degree of neutralization can calculate according to following formula:

Wherein x is degree of neutralization, i.e. the molar percentage that neutralized by stabilizing agent of tartaric acid, q _{stabilizing agent}the chemical valence of the metal cation of stabilizing agent, n _{stabilizing agent}the molal quantity of the stabilizing agent added in DATEM, n _winestone _acidthe tartaric molal quantity that preparation DATEM uses, m _{stabilizing agent}in being and the amount of the stabilizing agent that uses of DATEM (in gram), MW _{stabilizing agent}the molal weight (in gram/mol) of stabilizing agent, m _{tartaric acid}the tartaric amount (in gram) that preparation DATEM uses, MW _{tartaric acid}tartaric molal weight (in gram/mol).

As described herein, salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.In preferred at one, degree of neutralization can from 0.25% to 100%, preferably from 0.25% to 90%, preferably from 0.25% to 80%, preferably from 0.25% to 70%, preferably from 0.25% to 60%, preferably from 0.25% to 50%, preferably from 0.25% to 40%, preferably from 0.25% to 33%, preferably from 0.25% to 32.2%, preferably from 0.25% to 30%, preferably from 0.25% to 20%, preferably from 0.25% to 17%, preferably from 0.25% to 10%, preferably from 0.25% to 8%, preferably from 0.25% to 7%, preferably from 0.25% to 6.1%, preferably from 0.25% to 5%, preferably from 0.25% to 4%, preferably from 0.25% to 2%.

In another is preferred, degree of neutralization can from 0.5% to 100%, preferably from 0.5% to 90%, preferably from 0.5% to 80%, preferably from 0.5% to 70%, preferably from 0.5% to 60%, preferably from 0.5% to 50%, preferably from 0.5% to 40%, preferably from 0.5% to 33%, preferably from 0.5% to 32.2%, preferably from 0.5% to 30%, preferably from 0.5% to 20%, preferably from 0.5% to 17%, preferably from 0.5% to 10%, preferably from 0.5% to 8%, preferably from 0.5% to 7%, preferably from 0.5% to 6.1%, preferably from 0.5% to 5%, preferably from 0.5% to 4%, preferably from 0.5% to 2%.

In another is preferred, degree of neutralization can from 1% to 100%, preferably from 1% to 90%, preferably from 1% to 80%, preferably from 1% to 70%, preferably from 1% to 60%, preferably from 1% to 50%, preferably from 1% to 40%, preferably from 1% to 33%, preferably from 1% to 32.2%, preferably from 1% to 30%, preferably from 1% to 20%, preferably from 1% to 17%, preferably from 1% to 10%, preferably from 1% to 9%, preferably from 1% to 8%, preferably from 1% to 7%, preferably from 1% to 6.1%, preferably from 1% to 6%, preferably from 1% to 5%, preferably from 1% to 4%, preferably from 1% to 2%.

In another is preferred, degree of neutralization can from 2% to 100%, preferably from 2% to 90%, preferably from 2% to 80%, preferably from 2% to 70%, preferably from 2% to 60%, preferably from 2% to 50%, preferably from 2% to 40%, preferably from 2% to 33%, preferably from 2% to 32.2%, preferably from 2% to 30%, preferably from 2% to 20%, preferably from 2% to 17%, preferably from 2% to 10%, preferably from 2% to 9%, preferably from 2% to 8%, preferably from 2% to 7%, preferably from 2% to 6.1%, preferably from 2% to 6%, preferably from 2% to 5%, preferably from 2% to 4%.

In another is preferred, degree of neutralization can from 3% to 100%, preferably from 3% to 90%, preferably from 3% to 80%, preferably from 3% to 70%, preferably from 3% to 60%, preferably from 3% to 50%, preferably from 3% to 40%, preferably from 3% to 33%, preferably from 3% to 32.2%, preferably from 3% to 30%, preferably from 3% to 20%, preferably from 3% to 17%, preferably from 3% to 10%, preferably from 3% to 9%, preferably from 3% to 8%, preferably from 3% to 7%, preferably from 3% to 6.1%, preferably from 3% to 6%, preferably from 3% to 5%, preferably from 3% to 4%.

In a highly preferred embodiment, degree of neutralization is approximately 3.9%.

In one aspect, the amount of salt or alkali (c) is the gauge at least 0.1 % by weight based on DATEM.In one aspect, the amount of salt or alkali (c) is from 0.1 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.1 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.1 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is the gauge at least 0.2 % by weight based on DATEM.In one aspect, the amount of salt or alkali (c) is from 0.2 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.2 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.2 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is the gauge at least 0.3 % by weight based on DATEM.In one aspect, the amount of salt or alkali (c) is from 0.3 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.3 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt or alkali (c) is from 0.3 % by weight to 1.0 % by weight based on the gauge of DATEM.

In one aspect, the amount of salt (c) is the gauge at least 0.1 % by weight based on DATEM.In one aspect, the amount of salt (c) is from 0.1 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.1 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.1 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is the gauge at least 0.2 % by weight based on DATEM.In one aspect, the amount of salt (c) is from 0.2 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.2 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.2 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is the gauge at least 0.3 % by weight based on DATEM.In one aspect, the amount of salt (c) is from 0.3 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.3 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of salt (c) is from 0.3 % by weight to 1.0 % by weight based on the gauge of DATEM.

In one aspect, the amount of alkali (c) is the gauge at least 0.1 % by weight based on DATEM.In one aspect, the amount of alkali (c) is from 0.1 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.1 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.1 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is the gauge at least 0.2 % by weight based on DATEM.In one aspect, the amount of alkali (c) is from 0.2 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.2 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.2 % by weight to 1.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is the gauge at least 0.3 % by weight based on DATEM.In one aspect, the amount of alkali (c) is from 0.3 % by weight to 4.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.3 % by weight to 2.0 % by weight based on the gauge of DATEM.In one aspect, the amount of alkali (c) is from 0.3 % by weight to 1.0 % by weight based on the gauge of DATEM.

When salt is calcium salt, calcium salt can provide the amount of the calcium amount of the gauge at least 0.0115 % by weight based on DATEM to exist, such as to provide the gauge based on DATEM to exist from the amount of the calcium amount of 0.00115 % by weight to 4 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the calcium amount of 0.0115 % by weight to 4 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the calcium amount of 0.08 % by weight to 1.22 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the calcium amount of 0.12 % by weight to 0.24 % by weight, and preferably exist with the amount of the calcium amount of the gauge 0.16 % by weight based on DATEM.

When salt is sodium salt, sodium salt can provide the amount of the sodium amount of the gauge at least 0.0132 % by weight based on DATEM to exist, such as to provide the amount of the sodium amount of gauge from 0.0132 % by weight to 4.6 % by weight based on DATEM to exist, such as to provide the gauge based on DATEM to exist from the amount of the sodium amount of 0.09 % by weight to 1.4 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the sodium amount of 0.14 % by weight to 0.28 % by weight, and preferably to provide the amount of the sodium amount of the gauge 0.18 % by weight based on DATEM to exist.

When salt is sylvite, sylvite can provide the amount of the potassium amount of the gauge at least 0.0224 % by weight based on DATEM to exist, such as to provide the amount of the potassium amount of gauge from 0.0224 % by weight to 7.8 % by weight based on DATEM to exist, such as to provide the gauge based on DATEM to exist from the amount of the potassium amount of 0.16 % by weight to 2.38 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the potassium amount of 0.23 % by weight to 0.47 % by weight, and preferably to provide the amount of the potassium amount of the gauge 0.31 % by weight based on DATEM to exist.

When salt is magnesium salts, magnesium salts can provide the amount of the magnesium amount of the gauge at least 0.007 % by weight based on DATEM to exist, such as to provide the amount of the magnesium amount of gauge from 0.007 % by weight to 2.4 % by weight based on DATEM to exist, such as to provide the gauge based on DATEM to exist from the amount of the magnesium amount of 0.05 % by weight to 0.74 % by weight, such as to provide the gauge based on DATEM to exist from the amount of the magnesium amount of 0.07 % by weight to 0.15 % by weight, and preferably to provide the amount of the magnesium amount of the gauge 0.1 % by weight based on DATEM to exist.

It should be appreciated by those skilled in the art, in any stage of preparation process, stabilizing agent can be incorporated in emulsifier combination.Such as, stabilizing agent can be incorporated in emulsifier combination with the next stage:

A) before esterification forms DATEM

B) after esterification before deodorization

C) after deodorization

D) a), b), c) in one or more combination

In preferred at one, before esterification forms DATEM, stabilizing agent is added in acetic acid, tartaric acid and monoglyceride.

Provided by the invention stablizing can within the scope of series of temperature effectively.In one aspect, when emulsifier combination stores under 10 DEG C or higher temperature, provided by the invention stablizing is effective: such as 15 DEG C or higher temperature, such as 20 DEG C or higher temperature, such as 25 DEG C or higher temperature, such as 30 DEG C or higher temperature, the such as temperature of 10 DEG C to 100 DEG C, the such as temperature of 15 DEG C to 100 DEG C, the such as temperature of 20 DEG C to 100 DEG C, the such as temperature of 25 DEG C to 100 DEG C, the such as temperature of 30 DEG C to 100 DEG C, the such as temperature of 10 DEG C to 90 DEG C, the such as temperature of 15 DEG C to 90 DEG C, the such as temperature of 20 DEG C to 90 DEG C, the such as temperature of 25 DEG C to 90 DEG C, the such as temperature of 30 DEG C to 90 DEG C, the such as temperature of 10 DEG C to 80 DEG C, the such as temperature of 15 DEG C to 80 DEG C, the such as temperature of 20 DEG C to 80 DEG C, the such as temperature of 25 DEG C to 80 DEG C, the such as temperature of 30 DEG C to 80 DEG C, the such as temperature of 10 DEG C to 70 DEG C, the such as temperature of 15 DEG C to 70 DEG C, the such as temperature of 20 DEG C to 70 DEG C, the such as temperature of 25 DEG C to 70 DEG C, the such as temperature of 30 DEG C to 70 DEG C, the such as temperature of 10 DEG C to 60 DEG C, the such as temperature of 15 DEG C to 60 DEG C, the such as temperature of 20 DEG C to 60 DEG C, the such as temperature of 25 DEG C to 60 DEG C, the such as temperature of 30 DEG C to 60 DEG C, the such as temperature of 10 DEG C to 50 DEG C, the such as temperature of 15 DEG C to 50 DEG C, the such as temperature of 20 DEG C to 50 DEG C, the such as temperature of 25 DEG C to 50 DEG C, the such as temperature of 30 DEG C to 50 DEG C.

It should be appreciated by those skilled in the art, many emulsifier combinations store at low temperatures, are such as even low to moderate refrigerated storage temperature.This is normally in order to delay the deterioration of product.The application of the invention, in higher temperature, as under environment temperature, can store emulsifier combination.This end user being emulsifying agent all provides significant advantage in distribution chain and storage cost.

process in addition

After preparation DATEM, those skilled in the art can select DATEM product and DATEM product can have been carried out the process of packing in the mode meeting given customer requirement.

The DATEM product under room temperature being liquid or pasty state can be cooled and is contained in suitable container.

The DATEM product of fusing point more than 40 DEG C can be carried out misting cooling, delaminate or grind or be transformed into powder by other means.

annexing ingredient

Composition of the present invention can comprise one or more other components.

Anti-caking agent can be added subsequently, such as calcium carbonate, calcium silicates, tricalcium phosphate etc., to prevent powder agglomates in DATEM powder.

composition

Should be appreciated that the product that obtains by method of the present invention and/or contained in the present invention by the product that method of the present invention obtains.Therefore, in other, the invention provides

By the composition that method of the present invention obtains

Composition of the present invention can be used for the product preparing any amount, especially food such as bakery and whipping food.Therefore, in other, the invention provides:

The baked product comprising composition of the present invention or be made up of composition of the present invention.

The whipping food comprising composition of the present invention or be made up of composition of the present invention.

Present will only by way of example, with reference to following example, the present invention is described.

example

DATEM

Prepare following sample

Composition no	Stabilizing agent	Degree of neutralization %	Physical appearance
				1	Ca(OAc) ₂	0.18	Thin slice
2	NaOAc	0.18	Thin slice
				3	Mg(OAc) ₂·4H ₂O	0.18	Thin slice
4	KOAc	0.18	Thin slice
				5	Ca(OAc) ₂	4	Thin slice
6	NaOAc	4	Thin slice
				7	KOAc	4	Thin slice
8	Mg(OAc) ₂·4H ₂O	4	Thin slice
				9	Mg(OAc) ₂·4H ₂O	4	Liquid
10	Ca(OAc) ₂	4	Liquid
				11	Ca(OAc) ₂	4	Liquid
12	Ca(OAc) ₂	4	Liquid
				13	Magnesium lactate	4	Liquid
14	NaOAc	4	Liquid
				15	KOAc	4	Liquid
16	Ca(OAc) ₂	4	Liquid
				17	Ca(OAc) ₂	4	Liquid
18	Ca(OAc) ₂	4	Liquid
				19	Mg(OH) ₂	4	Liquid

20	Ca(OAc) ₂	4	Liquid
				21	Ca(OAc) ₂	4	Thin slice
22	Ca(OAc) ₂	6.1	Thin slice
				23	Ca(OAc) ₂	10	Thin slice
24	Ca(OAc) ₂	17	Thin slice
				25	Ca(OAc) ₂	32.2	Thin slice
26	Ca(OAc) ₂	2	Thin slice
				27	Ca(OAc) ₂	4	Thin slice
28	Ca(OAc) ₂	8	Thin slice
				29	Ca(OAc) ₂	15	Thin slice
30	Ca(OAc) ₂	30	Thin slice

composition 1-laboratory manual 2609/091 (comparison)

174.8g food-grade L-TARTARIC ACID is loaded together with 379.2g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2.8mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 149.3g distills hPKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) and 175.1g hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 0.168gCa (OAc) ₂(for neutralizing the H in the first reaction ₂sO ₄catalyst) and be fully mixed in the monoglyceride of thawing.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.Then 113.4g hardened palm oil (iodine number < 5) (deriving from Cargill Inc. (Cargil)) is added.

Finally making the product of steam by melting under 110 DEG C, 10 millibars, continuing 30 minutes, removing acetic acid residue.

By this operation, the product that free acetic acid content is less than 0.1% can be obtained.

The degree of neutralization of this product is:

composition 2-(comparison)

By the monoglyceride that 149.3g distills hPKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) and 175.1g hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 0.18gNaOAc (for neutralizing the H in the first reaction ₂sO ₄catalyst) and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of NaOAc.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.Then 113.4g hardened palm oil (iodine number < 5) (deriving from Cargill Inc. (Cargil)) is added.

The degree of neutralization of this product is:

composition 3-(comparison)

By the monoglyceride that 149.3g distills hPKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) and 175.1g hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 0.47gMg (OAc) ₂4H ₂o is (for neutralizing the H in the first reaction ₂sO ₄catalyst) and be fully mixed in the monoglyceride of thawing.

Containing Mg (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.Then 113.4g hardened palm oil (iodine number < 5) (deriving from Cargill Inc. (Cargil)) is added.

The degree of neutralization of this product is:

composition 4-(comparison)

By the monoglyceride that 149.3g distills hPKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) and 175.1g hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 0.86gKOAc (for neutralizing the H in the first reaction ₂sO ₄catalyst) and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of KOAc.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.Then 113.4g hardened palm oil (iodine number < 5) (deriving from Cargill Inc. (Cargil)) is added.

The degree of neutralization of this product is:

composition 5-laboratory manual 2609/93

249.5g food-grade L-TARTARIC ACID is loaded together with 541.2g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 462.9g distills hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 5.21gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.Then 162.8g hardened rapeseed oil (iodine number < 5) (deriving from Cargill Inc. (Cargil)) is added.

Product degree of neutralization is:

composition 6-laboratory manual 2609/132

150.00g food-grade L-TARTARIC ACID is loaded together with 321.0g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 334.4g distills hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.32gNaOAc and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of NaOAc.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.

Finally making the product of steam by melting under 110 DEG C, about 10 millibar, continuing 30 minutes, removing acetic acid residue.

Product degree of neutralization is:

composition 7-laboratory manual 2609/134

By the monoglyceride that 334.4g distills hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.98gKOAc and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of KOAc.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.

Product degree of neutralization is:

composition 8-laboratory manual 2609/136

By the monoglyceride that 334.4g distills hRKOSHER (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 5.08gMg (OAc) ₂4H ₂o is also fully mixed in the monoglyceride of thawing.

Containing Mg (OAc) ₂4H ₂the mixture of tartaric acid and acetic anhydride is added in the monoglyceride of O.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.

Product degree of neutralization is:

composition 9-laboratory manual 20140122-014-01

150.07g food-grade L-TARTARIC ACID is loaded together with 325.81g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.82g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 4.3gMg (OAc) ₂4H ₂o is also fully mixed in the monoglyceride of thawing.

Containing Mg (OAc) ₂4H ₂the mixture of tartaric acid and acetic anhydride is added in the monoglyceride of O.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.8g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.7g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 10-laboratory manual 20140122-014-02

150.11g food-grade L-TARTARIC ACID is loaded together with 325.89g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 178.47g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 1.60gCa (OAc) ₂and fully mix with the monoglyceride melted.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions, continue about 10 minutes.That is distilled by 178.47g comprises 1.60gCa (OAc) ₂monoglyceride bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads three neck round-bottomed flasks.103.0g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.8g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 11-laboratory manual 20140122-014-03

By the monoglyceride that 356.89g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 72.9g acetic anhydride, mixture is heated to 150 DEG C, continue 30 minutes, after being cooled to 80 DEG C, add 3.2gCa (OAc) ₂.Then the mixture of tartaric acid and acetic anhydride is added.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.22.5g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.81g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 12-laboratory manual 20140122-014-04

150.01g food-grade L-TARTARIC ACID is loaded together with 325.89g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.84g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 72.7g acetic anhydride, mixture is heated to 150 DEG C, continue 30 minutes, after being cooled to 80 DEG C, add 3.2gCa (OAc) ₂.Mixture is divided into two equal portions, the mixture of tartaric acid and acetic anhydride is joined in a copy of it.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions, continue about 10 minutes.By reactant mixture second half ( bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) and containing Ca (OAc) ₂acetic anhydride) load three neck round-bottomed flasks.22.53g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue about 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.69g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 13-laboratory manual 20140225-008-1

150.03g food-grade L-TARTARIC ACID is loaded together with 325.89g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.91g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 4.3g magnesium lactate and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of magnesium lactate.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.9g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.8g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 14-laboratory manual 20140225-008-2

150.05g food-grade L-TARTARIC ACID is loaded together with 331.01g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 1mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.18g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.2gNaOAc and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of NaOAc.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.82g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.9g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 15-laboratory manual 20140225-008-3

By the monoglyceride that 356.18g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.9gKOAc and be fully mixed in the monoglyceride of thawing.

Add the mixture of tartaric acid and acetic anhydride in containing the monoglyceride of KOAc.Reactant mixture is heated to about 110 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.82g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.9g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 16-laboratory manual 20140310-016-01

150.04g food-grade L-TARTARIC ACID is loaded together with 325.87g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.82g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.20gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Will containing Ca (OAc) ₂monoglyceride add in the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.84g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.9g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 17-laboratory manual 20140310-016-02

150.04g food-grade L-TARTARIC ACID is loaded together with 325.87g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.Reduce pressure gradually to distill out acetic acid, continue about 10 minutes.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.84g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.9g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 18-laboratory manual 20140310-016-04

150.04g food-grade L-TARTARIC ACID is loaded together with 325.87g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.By the monoglyceride that 356.82g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.

The mixture of tartaric acid and acetic anhydride is added in monoglyceride.Add 3.20gCa (OAc) ₂and be fully mixed in reactant mixture.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.84g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.9g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 19-laboratory manual 20140403-001-02

150.02g food-grade L-TARTARIC ACID is loaded together with 325.81g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.By the monoglyceride that 356.84g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.

The mixture of tartaric acid and acetic anhydride is added in monoglyceride.Add 1.20gMg (OH) ₂and be fully mixed in reactant mixture.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.82g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.7g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 20-laboratory manual 2609/122

150.0g food-grade L-TARTARIC ACID is loaded together with 325.8g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 2mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 356.8g distills bP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.2gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.102.8g acetic anhydride is added in reactant mixture, reactant mixture is heated to 130 DEG C, continue 30 minutes.115 DEG C, after (115-15 millibar) distills out acetic acid under reduced pressure, then add 93.7g sunflower oil (deriving from Cargill Inc. (Cargil)).

Product degree of neutralization is:

composition 21-laboratory manual 2697/186

99.0g food-grade L-TARTARIC ACID is loaded together with 212.6g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.67mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 133.2g distills hRKOSHER and 217.0g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 2.13gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Containing Ca (OAc) ₂monoglyceride in add the mixture of tartaric acid and acetic anhydride.Reactant mixture is heated to about 105 DEG C, (115 millibars-15 millibars) distill out acetic acid at reduced pressure conditions.

Product degree of neutralization is:

composition 22-laboratory manual 2697/187

99.0g food-grade L-TARTARIC ACID is loaded together with 215.6g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.67mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 133.0g distills hRKOSHER and 217.1g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 3.2gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 23-laboratory manual 2697/188

99.1g food-grade L-TARTARIC ACID is loaded together with 212.5g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.67mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 133.0g distills hRKOSHER and 217.4g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 5.2gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 24-laboratory manual 2697/189

99.4g food-grade L-TARTARIC ACID is loaded together with 213.6g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.67mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 133.1g distills hRKOSHER and 216.8g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 8.9gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 24-laboratory manual 2697/190

99.1g food-grade L-TARTARIC ACID is loaded together with 212.3g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.67mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 132.0g distills hRKOSHER and 215.1g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 16.7gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 25-laboratory manual 2697/191

134.6g food-grade L-TARTARIC ACID is loaded together with 288.56g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.90mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 114.6g distills hRKOSHER and 185.6g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 1.4gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 26-laboratory manual 2697/192

134.4g food-grade L-TARTARIC ACID is loaded together with 288.0g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.90mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 114.0g distills hRKOSHER and 185.4g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 2.8gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 27-laboratory manual 2697/193

134.8g food-grade L-TARTARIC ACID is loaded together with 287.3g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.90mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 113.6g distills hRKOSHER and 185.1g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 5.7gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 27-laboratory manual 2697/194

134.5g food-grade L-TARTARIC ACID is loaded together with 288.5g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.90mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 113.2g distills hRKOSHER and 184.3g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 10.6gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

composition 28-laboratory manual 2697/195

134.5g food-grade L-TARTARIC ACID is loaded together with 287.9g acetic anhydride and is equipped with in the 1L tri-neck round-bottomed flask of overhead type stirrer, condenser and thermometer.Slowly add the 1%H that 0.90mL is dissolved in acetic acid ₂sO ₄(v/v), stir with overhead type stirrer simultaneously.Reactant mixture is heated to 110 DEG C, continues about 10 minutes.

By the monoglyceride that 112.5g distills hRKOSHER and 182.6g be mono--double glyceride HP (deriving from Du Pont's nutrients biological scientific company (DuPontNutritionBiosciencesApS, Denmark) of Denmark) loads another three necks round-bottomed flask.Add 10.6gCa (OAc) ₂and be fully mixed in the monoglyceride of thawing.

Product degree of neutralization is:

headspace analysis

By headspace analysis, the mensuration of smell/acetic acid content is carried out to sample.Method of testing details is as follows.

100mg sample is transferred in 22ml bottle, at 30 DEG C, balance 5 minutes.Subsequently, adopt SPME principle (SPME), at 30 DEG C, from gas phase, extract volatile matter, continue 20 minutes.Then at 260 DEG C, at the injection port place of GC/MS system by volatile matter thermal desorption, and obtain chromatogram.Draw acetic acid response (compared to response during t=0, in chromatogram acetic acid peak under area) with the relation of time.

result

Depict the headspace analysis result that sample 1 and sample 5 are passed in time.Result is shown in Figure 1.

Can be clear that, the stablizing effect with the example 5 of higher calcium salt content is obviously better than the example 1 with lower calcium salt content.In the time of about 4 weeks, the acetic acid content of non-stabilized sample raises, and due to the smell that acetic acid produces, it is unacceptable that this sample is used in some food applications.

Provide the final headspace analysis result of multiple other composition in table 1 below, comprising storing the result after reaching for about 1 year.

table 1

Composition no	Number of days before test	Acetic acid content (%)
			1 (comparison)	28	0.67
6	325	0.03
			7	324	0.16
8	322	0.02
			9	93	0.04
13	58	0.13
			14	58	0.4
15	58	0.23
			19	58	0.03
20	339	0.1

Compared to non-stabilized DATEM, the smell of product of the present invention significantly reduces and stability at ambient temperature significantly improves, which improve the bin stability of DATEM product itself, improve the actual manageability of DATEM product in food applications, thus obtain better working environment, food quality and shelf-life.

The all publications mentioned in description are above incorporated to herein all by reference.When not deviating from scope and spirit of the present invention, those skilled in the art can expect the various modifications and variations of the inventive method described herein and system apparently.Although invention has been described in conjunction with concrete preferred embodiment, should be understood that the present invention that prescription is protected should be limited to these specific embodiments irrelevantly.In fact, the various amendments to embodiment of the present invention described herein that chemistry or various equivalent modifications are expected apparently, are also considered as falling in the scope of following claims.

Claims

1. an emulsifier combination, described emulsifier combination comprises:

The diacetyl tartrate (DATEM) of (a) list and two glyceride;

B (), based on the gauge of described DATEM, is less than the free acetic acid of the amount of 0.4 % by weight; With

(c) salt or alkali, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.

2. emulsifier combination according to claim 1, the amount of wherein said free acetic acid is be less than 0.1 % by weight based on the gauge of described DATEM.

3. emulsifier combination according to claim 1 and 2, wherein said salt or alkali (c) can be one or more carboxylic acid donate metallic ions, to form the salt of one or more carboxylic acids described, one or more carboxylic acids wherein said are selected from DATEMI, DATEMII, DATEMIII, DATEMIV, its position isomer, free acetic acid and composition thereof.

4. according to emulsifier combination in any one of the preceding claims wherein, wherein said salt (c) is slaine, described slaine can be one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM.

5., according to emulsifier combination in any one of the preceding claims wherein, the salt that wherein said salt or alkali (c) are metal or alkali, described metal is selected from the 1st race of the periodic table of elements, the 2nd race and Al of the periodic table of elements.

6., according to emulsifier combination in any one of the preceding claims wherein, the salt that wherein said salt or alkali (c) are metal or alkali, described metal is selected from lithium, sodium, potassium, magnesium, calcium and aluminium.

7., according to emulsifier combination in any one of the preceding claims wherein, wherein said salt (c) is calcium salt.

8., according to emulsifier combination in any one of the preceding claims wherein, wherein said salt (c) is the salt of acid, and described acid is selected from formic acid, acetic acid, propionic acid and lactic acid.

9., according to emulsifier combination in any one of the preceding claims wherein, wherein said salt or alkali (c) are selected from magnesium hydroxide, calcium acetate, sodium acetate, magnesium acetate, magnesium lactate, potassium acetate and aluminium acetate and composition thereof.

10., according to emulsifier combination in any one of the preceding claims wherein, wherein said salt (c) is calcium acetate.

11. according to emulsifier combination in any one of the preceding claims wherein, and the amount of wherein said salt or alkali (c) is the gauge at least 0.1 % by weight based on described DATEM.

12. according to emulsifier combination in any one of the preceding claims wherein, and the amount of wherein said salt (c) is from 0.1 % by weight to 1.0 % by weight based on the gauge of described DATEM.

13. according to emulsifier combination in any one of the preceding claims wherein, and wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 2mol%.

14. according to emulsifier combination in any one of the preceding claims wherein, and wherein said DATEM comprises the tartaric acid of 10 % by weight to 30 % by weight.

15. according to emulsifier combination in any one of the preceding claims wherein, and after wherein storing 28 days at 30 DEG C, the amount of the free acetic acid existed in described composition adds less than 100%.

16. 1 kinds of methods preparing emulsifier combination, described emulsifier combination comprises

The diacetyl tartrate (DATEM) of (a) list and two glyceride;

(c) salt or alkali, wherein said salt or alkali can for one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%

Described method comprises

I) diacetyl tartrate (DATEM) that is single and two glyceride is provided;

Ii) optionally deodorization is carried out to described DATEM, make described DATEM comprise gauge based on described DATEM, be less than the free acetic acid of the amount of 0.4 % by weight; With

Iii) at step I i) before or after, described DATEM and salt or alkali are merged, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM.

17. methods according to claim 16, wherein carry out step I i) deodorization is carried out to described DATEM, make it comprise gauge based on described DATEM, be less than the free acetic acid of the amount of 0.4 % by weight.

18. methods according to claim 16 or 17, wherein before step (ii), merge described DATEM and described salt or alkali.

19. methods according to claim 16,17 or 18, is characterized in that the feature according to any one of claim 2 to 15.

20. 1 kinds of emulsifier combinations, described emulsifier combination is by obtaining according to claim 16 to the method according to any one of 19 or obtaining by described method.

21. 1 kinds of food, described food product packets containing the emulsifier combination limited any one of claim 1 to 15,19 or 20, or is prepared by described emulsifier combination.

22. food according to claim 21, wherein said food is baked product.

The purposes of the diacetyl tartrate (DATEM) for stable list and two glyceride of 23. salt or alkali, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM.

The purposes for reducing or suppress the middle acetic acid release of the diacetyl tartrate (DATEM) of list and two glyceride of 24. salt or alkali, wherein said salt or alkali can be one or more carboxylic acid donate metallic ions existed in described DATEM, to form the salt of the described carboxylic acid be present in described DATEM.

25. purposes according to claim 23 or 24, wherein said salt or alkali exist to provide the amount of the degree of neutralization of at least 0.25mol%.